Top 6 Marriage Proposals Gone Wrong

Posted By Ben Goulding, 10 March, 2010 | permalink

Becoming engaged is meant to one of the best days in a person’s life, but when something goes wrong with the proposal, it can end up being one of the worst. Here are the top 6 marriage proposals gone wrong.

#1 Man Dropped Ring On Brooklyn Bridge

What was meant to be an elaborate marriage proposal turned out to be a nightmare for one man and his partner.

Don Walling and his girlfriend, Gina Pellicani, had gone to dinner with family to celebrate his 29th birthday. Afterwards, they decided to walk across the Brooklyn Bridge where Don would propose.

With a relative filming the event, Don got down on one knee, took out the ring box and opened it, but to his horror the engagement ring fell out of the box and into the New York traffic below.

Don scaled the side of the bridge as motorists, thinking he was suicidal, begged him not to jump. Next, a suicide prevention van pulled up and police stopped the traffic.

When the ring was eventually found, the platinum band was damaged but all the stones were fine, luckily… Not really.

#2 Rejected in Front of a Sell-Out Basketball Stadium on National TV


(Youtube Link)

This guy had it all planned out. What better way than proposing to the one you love in front of a stadium full of people and a national television audience? How could she possible say no? Watch the video to see how it turned out.

#3 Engagement Ring Flies Away Inside Helium Balloon

Lefkos Hajji wanted to do something creative when he proposed to his girlfriend. The idea he came up with was to put the engagement ring inside a helium balloon, give it to his loved one and then pop the question, literally. Unfortunately, it didn’t quite turn out like that.

Lefkos asked a florist to place his $12,000 diamond engagement ring inside a helium balloon, but as he left the shop a gust of wind pulled it from his hand and it soared into the sky.

Despite chasing it for nearly two hours in his car, Lefkos eventually had to give up the pursuit and the ring or balloon were never seen again.

Needless to say, when Lefkos told his girlfriend, she went mad and refused to talk to him until he got her a new ring.


#4 Live TV Show Proposal is Painfully Awkward


(Youtube Link)

When this guy decided to propose on live television, he envisioned it to be the best day of his life, but it ended up being probably the worst. Check out the video to feel his pain and everyone else’s awkwardness.

#5 Woman Swallows Engagement Ring Hidden in Milkshake

Reed Harris did something different for his proposal, by hiding the ring in a Wendy’s Frosty milkshake and then giving it to his girlfriend.

However, as she ate the milkshake, girlfriend, Kaitlin Whipple, didn’t find anything and by the time she had finished there wasn’t a ring in the glass.

It turned out that Kaitlin had ate the ring without noticing. How could she possibly do this? Well, the other women that were with her made the mistake of challenging her to a milkshake eating race, eager to speed up the process of finding the ring. Unfortunately, Kaitlin grabbed a spoon and wolfed down the entire contents of the cup, including the ring!

#6 Valentines Day Public Hockey Match Rejection


(Youtube Link)

Proposing in public is a risky thing to do, because if she says ‘no’, then you’re going to be totally humiliated. What could possibly be worse than that? How about if it was on Valentines Day? Well, that’s what happened to this guy in New York. Ouch!

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